What is an Entrepreneurial Pirate?
An Entrepreneurial Pirate is someone who maximizes potential and opportunities. They are captains of their ship and take responsibility for their own lives. They take action and set sail, navigating with intent. They aren’t afraid of making mistakes and see them as learning opportunities. They are always focused on finding the treasure.
Entrepreneurial pirates thrive in companies like ours especially given the values of “think big,” “move fast,” and “keep growing.” Here are five steps to becoming an entrepreneurial pirate.
Step 1 – Be the Captain of your ship
Entrepreneurial Pirates own and drive to the outcome. Identifying your ideal outcomes early on in everything you do will help you avoid a checkbox mentality. By tying your outcome to a success metric from the beginning instead of a release date or exact feature set (or similar), you may find yourself making different choices to meet your outcome metric goal.
One of my favorite examples of this is the Security Dashboard and DWM release. We hypothesized from user interviews and usability testing that the feature itself was a significant value-add to the end user experience. We expected to have high adoption (input metric) that would lead to conversion (output metric). What surprised us was that people weren’t using it, and adoption was low.
So instead of putting effort towards fast-follow feature improvements, we focused on driving up our input metrics for product usage and adoption, working collaboratively with marketing, and making some small, targeted product changes like adding “new” to the main navigation. Eventually, after iterations, we saw our output metric (conversion) move.
Step 2 – Take action and set sail
There is no pause. Most decisions are two-way doors and can be undone if they turn out to be mistakes. If you are stuck, bring in others who can get you unstuck – brainstorm with a cross-functional team, research best practices, understand your competitors, and create a test plan. The key is to do something and to keep your momentum towards your outcome. Sometimes, in a remote world, we get stuck just waiting to have a meeting with the right people before sign-off. Don’t get bogged down by this. Instead, take advantage of our writing culture and create a 1-pager explaining what you are trying to accomplish, and outline steps needed to get there. Ask people to comment directly in the document, then revise and share again. This approach could save you weeks and allow you to set sail towards your goal faster.
Step 3 – Navigate with intent
Know your inputs to your output metric. Rarely can a single team deliver fully to move an output metric - collaboration is necessary and usually fruitful. Identify your baseline and create dashboards to track success for your cross-functional team. Stay focused. Ask yourself, “what is the one thing I can do this month weekday to help me achieve the output.” Check out a great book – The One Thing.
Successful entrepreneurs are known to be high intent and to stop at nothing to achieve their goal. A podcast that I love is “How I Built It” with Guy Raz. It highlights entrepreneurs and their stories. One that sticks with me is Spanx: Sara Blakely episode. She did her early research by going into a department store and interviewing sales associates to determine if customers would be interested in her product - no scheduled interviews, no “thank you” gifts, no recordings. Entrepreneurs and especially Entrepreneurial Pirates must be willing to navigate outside of the lines of convention - the good news is that we are selling software not hosiery!
Step 4 – Entrepreneurial Pirates aren’t afraid
The path to conquering fear requires practice failing and a belief that “you can do it.”
Try out failure! I find that designers are the most comfortable of the groups that I have worked with over time with failure. Maybe this is what keeps them so creative? Designers are known for delivering three versions of a design, knowing that only one will be picked and used - no doubt one will effectively be a failure. Even when a “winner” is chosen, there is usually lots of feedback and many design versions before it is finished. Think of your failures as learning opportunities and iterations to the final product.
You can do it! Become your own biggest supporter - start by shutting down any internal dialog working against you - free yourself from thinking traps. Check out this article to learn to take control of that internal dialog and learn to use it to your advantage.
Step 5 – “X” marks the spot
Sometimes you need to play the long game to get to your treasure. Forming and evolving a product, team, or process may take time. Be sure to set short-term goals for yourself and stay focused on the prize. What is the treasure you want to uncover?
A few reference docs:
https://zerodean.com/pirates-vs-zombies/new-pirates-in-detail/